WO1989001003A1 - Compositions de poly(arylether sulfone) a fluidite amelioree - Google Patents

Compositions de poly(arylether sulfone) a fluidite amelioree Download PDF

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Publication number
WO1989001003A1
WO1989001003A1 PCT/US1988/002541 US8802541W WO8901003A1 WO 1989001003 A1 WO1989001003 A1 WO 1989001003A1 US 8802541 W US8802541 W US 8802541W WO 8901003 A1 WO8901003 A1 WO 8901003A1
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Prior art keywords
poly
aryl ether
ether sulfone
composition
formula
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Application number
PCT/US1988/002541
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English (en)
Inventor
James E. Harris
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Amoco Corporation
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Publication date
Application filed by Amoco Corporation filed Critical Amoco Corporation
Priority to AT88907470T priority Critical patent/ATE94887T1/de
Publication of WO1989001003A1 publication Critical patent/WO1989001003A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/06—Polysulfones; Polyethersulfones

Definitions

  • This invention is directed to immiscible poly(aryl ether sulfone) blends possessing improved flow properties.
  • the novel compositions contain (a) from about 80 to about 99 percent by weight of a poly(aryl ether sulfone) having a second order glass transition temperature (Tg) higher than about 240oC, and (b) from about 1 to about 20 percent by weight of a second poly(aryl ether sulfone) having a Tg lower than about 225oC.
  • Tg second order glass transition temperature
  • Poly(aryl ether sulfones) have been known for about two decades; they are tough linear polymers that possess a number of attractive features such as excellent high temperature resistance, good electrical properties, and very good hydrolytic stability. Two poly(aryl ether sulfones) are commercially available. A poly(aryl ether sulfone) is available from Imperial Chemical Industries Limited. It has the formula (1)
  • H is produced by polycondensation of 4-(4'-chloro- phenylsulfonyl) phenol, as described in British Patent Specification No. 1,153,035.
  • the polymer contains no aliphatic moieties and has a heat deflection temperature of approximately 210oC.
  • Another commercial poly- (aryl ether) is available from Amoco Performance Products, Inc. under the trademark. UDEL ® . It corresponds to formula (2) and has a heat deflection temperature of about 180°C.
  • Polymer (2) is prepared via the nucleophilic poly- condensation reaction of 2,2-bis(4-hydroxy-phenyl) propane (“bisphenol-A”) with 4,4'-dichlorodiphenyl sulfone.
  • bisphenol-A 2,2-bis(4-hydroxy-phenyl) propane
  • 4-Dichlorodiphenyl sulfone 4,4'-dichlorodiphenyl sulfone.
  • This, method described by Johnson et al., Journal of Polymer Science, A-1, Vol. 5, 1967, pp. 2415-2427, and Johnson et al., U. S. Patent Nos. 4,107,837 and 4,175,175, has been shown to be quite general and applicable for the synthesis of a broad range of other poly(aryl ether sulfones) (hereinafter called PAE's).
  • PAE's poly(aryl ether sulfones)
  • Materials (1) and (2) display relatively low glass- transition and, hence, low heat distortion temperatures.
  • the drawback is serious, since it makes the two polymers unsuitable in applications where a high Tg is important. Such applications include, for example, the area of composites which often require a matrix capable of maintaining structural integrity at relatively high temperatures.
  • numerous poly(aryl ether sulfones) having high Tg's have been prepared. Of particular interest among these latter polymers are those containing the 4,4'-bis(phenylsulfonyl)biphenyl units (3):
  • Ar is defined as a diphenylene or naphthylene radical or a polynuclear divalent radical of the formula:
  • Z is a divalent aliphatic, cycloaliphatic or arylaliphatic radical containing 1 to 8 carbon atoms or -O-, -S-, -SO-, -SO 2 -, or -CO-.
  • U. S. Patent No. 3,634,355 describes a number of polymers prepared from 4,4'-bis(4-chlorophenylsulphonyl)- biphenyl (5).
  • Example 16 depicts the polymer containing units (6) and (7) is a 4:1 molar ratio.
  • Example 17 shows the same structure, except that units (6) and (7) are present in a 1:1 ratio.
  • poly(aryl ether sulfones) displaying high glass transition temperatures are, for example, those containing terphenylene, naphthylene, anthracenylene and fluorene-9,9-bis(phenylene) units (8):
  • immiscible blends containing (a) from about 80 to about 99 percent by weight, preferably from about 85 to about 98 percent by weight, of a poly(aryl ether sulfone) having a second order glass transition temperature (Tg) higher than about 240oC, and (b) from about 1 to about 20 percent by weight preferably from about 2 to about 15 percent by weight of a second poly (aryl ether sulfone) having a Tg lower than about 225°C, display vastly improved melt-flow properties. It is unexpected that the compositions retain the excellent mechanical properties of the constituents. Moreover, the heat distortion temperature of the high Tg material remains practically unaffected by the addition of the lower Tg polymer.
  • the two poly (aryl ether sulfones) be immiscible.
  • a two-phase immiscible blend is demonstrated by the blend having two distinct glass transition temperatures (Tg).
  • Tg glass transition temperatures
  • the poly(aryl ether sulfones) having second order glass transition temperatures greater than about 240°C are based on the monomers of formula (9) where X is a halogen, preferably chlorine or fluorine, or a hydroxyl group; Ar is a divalent aromatic radical selected from the group of
  • X halogen or hydroxyl (9) biphenylene (10), terphenylene (11), naphthylene (12), anthracenylene (13), and fluorene-9,9-bis(phenylene) (8);
  • R 1 and R 2 are inert substituents such as hydrogen or C 1 to C 4 alkyl or alkoxy groups; they can be the same or different.
  • the nucleophilic polycondensation of (14) with a dihydric phenol and an activated dihalobenzenoid compound offers these high Tg products.
  • the high Tg materials contain at least 50 mole percent of units (15).
  • the dihydric phenols useful in the instant invention are preferably weakly acidic dinuclear phenols such as, for example, the dihydroxy-diphenyl alkanes or the nuclear halogenated derivatives thereof, such as, for example, the 2,2-bis(4-hydroxyphenyl)propane, 1,1-bis(4- hydroxyphenyl)2-phenyl ethane, bis(4-hydroxyphenyl)methane, or their chlorinated derivatives containing one or two chlorines on each aromatic ring.
  • Other materials also termed appropriately bisphenols are also highly valuable and preferred. These materials are the bisphenols of a symmetrical or unsymmetrical joining group, as for example, ether oxygen
  • Ar 1 is an aromatic group and preferably is a phenylene group
  • R 3 and R' 3 can be the same or different inert substituent groups such as alkyl groups having from 1 to 4 carbon atoms, aryl, halogen atoms, i.e., fluorine, chlorine, bromine or iodine, or alkoxy radicals having from 1 to 4 carbon atoms
  • the d , s are independently integers having a value of from 0 to 4, inclusive
  • R 4 is representative of a bond between aromatic carbon atoms as in dihydroxy-diphenyl, or is a divalent radical.
  • radicals such as -O-, -S-, -S-S-, -SO-, -SO 2
  • divalent hydrocarbon radicals such as alkylene, alkylidene, cycloalkylene, cycloalkylidene, or the halogen, alkyl, aryl or like substituted alkylene, alkylidene and cycloaliphatic radicals as well as aromatic radicals and radicals fused to both Ar 1 groups.
  • dihydric polynuclear phenols examples include, among others, the bis-(hydroxyphenyl) alkanes such as
  • 2,4'-dihydroxydiphenylmethane bis-(2-hydroxyphenyl)methane, bis-(4-hydroxyphenyl)methane, bis(4-hydroxy-2,6-dimethyl-3-methoxyphenyl)- methane 1,1-bis-(4-hydroxyphenyl)ethane 1,2-bis-(4-hydroxyphenyl)ethane, 1,1-bis-(4-hydroxy-2-chlorophenyl)ethane, 1,1-bis-(3-methyl-4-hydroxyphenyl)propane,
  • 4,4'-dihydroxy-2,6-dimethyldiphenyl ether bis-(4-hydroxy-3-isopropylphenyl)ether, bis-(4-hydroxy-3-chlorophenyl)ether, bis-(4-hydroxy-3-fluorophenyl)ether, bis-(4-hydroxy-3-bromophenyl)ether, bis-(4-hydroxynaphthyl)ether, bis-(4-hydroxy-3-chloronaphthyl)ether, and 4,4'-dihydroxy-3,6-dimethoxydiphenyl ether.
  • diphenols are, for example, the naph- thalenediols and the mononuclear diphenols such as hydroguinone or resorcinol.
  • Dihydroxybiphenyls, such as 4,4'-biphenol, are also very useful.
  • dinitrobenzenoid compounds are also suitable for "the purposes of the instant invention. Any dihalobenzenoid or dinitrobenzenoid compound or mixtures thereof can be employed in this invention which compound or compounds has the two halogens or nitro-groups bonded to benzene rings having an electron withdrawing group in at least one of the positions ortho or para to the halogen or nitro group.
  • the dihalobenzenoid or dinitrobenzenoid compound can be either mononuclear, where the halogens or nitro groups are attached to the same benzenoid ring; or polynuclear where they are attached to different benzenoid rings, as long as there is an activating electron withdrawing group in the ortho or para position of that benzenoid nucleus.
  • Fluorine and chlorine substituted benzenoid reactants are preferred; the fluorine compounds for fast reactivity and the chlorine compounds for their inexpensiveness.
  • Fluorine substituted benzenoid compounds are most preferred, particularly when there is a trace of water present in the polymerization reaction system. However, this water content should be maintained below about 1 percent and preferably below 0.5 percent for best results.
  • an electron withdrawing group is employed as the activator group in these compounds. It should be, of course, inert under the reaction conditions, but otherwise its structure is not critical. Preferred are the strongly activating groups such as the sulfone group
  • the ring contain no electron supplying groups on the same benzenoid nucleus as the halogen or nitro group; however, the presence of other groups on the nucleus or in the residuum of the compound can be tolerated.
  • the activating groups can be basically either of two types:
  • polyarylene polyether polymers of this invention are prepared by methods well known in the art as for instance the one-step reaction of a double alkali metal salt of a dihydric phenol with a dihalobenzenoid compound in the presence of specific liquid organic sulfoxide or sulfone solvents under substantially anhydrous conditions. Catalysts are not necessary for this reaction.
  • the polymers may also be prepared in a two-step process in which a dihydric phenol is first converted in situ in the primary reaction solvent to the alkali metal salt by the reaction with the alkali metal, the alkali metal hydride, alkali metal hydroxide, alkali metal alkoxide or the alkali metal alkyl compounds.
  • the alkali metal hydroxide is employed.
  • the dialkali metal salts of the dihydric phenol are admixed and reacted with the dihalobenzenoid or dinitrobenzenoid compound.
  • polyethers may be prepared by the procedure described in, for example, U. S. Patent No. 4,176,222 in which at least one bisphenol and at least one dihalobenzenoid compound are heated at a temperature of from about 100° to about 400°C with a mixture of sodiuia carbonate or bicarbonate and a second alkali metal carbonate or bicarbonate having a higher atomic number than that of sodium.
  • polyethers may be prepared by the procedures described in Canadian Patent No. 847,963 wherein the bisphenol and dihalobenzenoid compound are heated in the presence of potassium carbonate using a high boiling solvent such as diphenylsulfone.
  • Halophenols or nitrophenols wherein the halogen or nitro group is activated by an electron withdrawing group in the ortho- and/or para positions can also be used for the preparation of the poly(aryl ether sulfones).
  • the halophenols or nitrophenols can be used alone or in conjunction with a diphenol and a dihalo- or dinitro- benzenoid compound as defined above.
  • the electrophilic polymerizations are performed in the presence of typical Friedel-Crafts catalysts such as ferric chloride, aluminum chloride, ferric bromide, boron trifluoride, and the like.
  • typical Friedel-Crafts catalysts such as ferric chloride, aluminum chloride, ferric bromide, boron trifluoride, and the like.
  • solvents such as chlorinated hydrocarbons, nitrobenzene, arochlor, dimethyl sulfone, etc. are useful.
  • Temperatures of up to 250oC, and even higher are preferably employed when high molecular weight polymers are desired.
  • the preferred high Tg poly(aryl ether sulfones) are (19), and those based on (5) and the dihydric phenols (20), (21), (22), (23), and (24).
  • poly(aryl ether sulfones) having second order glass transition temperatures lower than about 225oC are obtained by the nucleophilic polycondensation of 4,4'- dichlorodiphenyl sulfone (25) with ⁇
  • X' is selected from the group of hydrocarbon radicals such as alkylene and alkylidene radicals having up to and inclusive 8 carbon atoms, cycloalkylene and cycloalkylidene radicals having up to and inclusive 9 and the radicals the R 5 's are C 1 to C 4 alkyl or alkoxy radicals or halogen atoms and can be the same or different; the R 6 's are hydrogen or C 1 to C 4 alkyl radicals or halogen atoms; they can be the same or different.
  • hydrocarbon radicals such as alkylene and alkylidene radicals having up to and inclusive 8 carbon atoms, cycloalkylene and cycloalkylidene radicals having up to and inclusive 9 and the radicals the R 5 's are C 1 to C 4 alkyl or alkoxy radicals or halogen atoms and can be the same or different; the R 6 's are hydrogen or C 1 to C 4 alkyl radicals or halogen atoms
  • the low Tg poly(aryl ether sulfones) are prepared using methods that are similar to those used for the preparation of their high Tg counterparts.
  • the preferred low Tg poly(aryl ether sulfone) is rep- resented by formula (2).
  • compositions of this invention are prepared by any conventional mixing method.
  • a preferred method comprises mixing the two poly(aryl ether sulfones) in powder or granular form in an extruder and extruding the mixture into strands, chopping the strands into pellets and molding the pellets into the desired article.
  • the compositions of this invention may include mineral fillers such as carbonates including chalk, calcite and dolomite; silicates including mica, talc, wollastonite, silicon dioxide; glass spheres; glass powders; aluminum; clay; quartz; and the like. Also, reinforcing fibers such as fiberglass, carbon fibers, and the like may be used.
  • compositions may also include additives such as titanium dioxide; thermal stabilizers, ultraviolet light stabilizers, plasticizers, and the like.
  • additives such as titanium dioxide; thermal stabilizers, ultraviolet light stabilizers, plasticizers, and the like.
  • the compositions of this invention may be fabricated into any desired shape, i.e., moldings, coatings, films, or fibers. They are particularly desirable for use as electrical insulation for electrical conductors.
  • the material was fluxed in a Brabender Plasticorder mixer at 360oC for about 5 minutes.
  • the melt flow index of the copolymer at 380°C and 44 psi was measured according to ASTM D1238 and is given in Table I.
  • the copolymer resin was placed in a 4x4x0.020-inch cavity mold and compression molded in a South Bend hydraulic press whose jaws had been electrically heated to about 375°C.
  • the 0.020-inch thick compression molded sheet was shear cut into one-eighth inch wide strips.
  • the heat deflection temperature at 264 psi (ASTM D648) was estimated as follows:
  • the modulus-temperature curve and Tg were measured for specimens shear cut from the compression molded sheet according to the method described in Olabisi, et al., Polymer-Polymer Miscibility, Academic Press, NY, page 126.
  • the HDT was taken as the temperature at which the tensile modulus dropped to 100,000 psi as described by M. T. Takemori, Soc. Plastics Eng., Proceedings of 36th ANTEC Conf., April 1978, pp. 216-219.
  • the Tg and HDT are given in Table I.
  • EXAMPLE 1 85 weight percent of the poly(aryl ether sulfone) of Control A was mixed with 15 weight percent of polysulfone with a Tg of 185oC of the structure
  • Control B 85 weight percent of the poly(aryl ether sulfone) of Control B was mixed with 15 weight percent of polysulfone with a Tg of 185oC of the structure

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyethers (AREA)

Abstract

Des mélanges non miscibles de poly(aryléther sulfone) présentent une fluidité améliorée. Ces compositions nouvelles contiennent (a) entre 80 et 99 % en poids environ d'une poly(aryléther sulfone) ayant une température de transition vitreuse de deuxième ordre (Tg) supérieure à 240°C environ, et (b) entre 1 et 20 % en poids environ d'une deuxième poly(aryléther sulfone) ayant une Tg inférieure à 225°C environ. Ces compositions conservent les caractéristiques très attrayantes de leurs constituants et présentent des propriétés mécaniques et une résistance à la chaleur excellentes.
PCT/US1988/002541 1987-07-27 1988-07-27 Compositions de poly(arylether sulfone) a fluidite amelioree WO1989001003A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88907470T ATE94887T1 (de) 1987-07-27 1988-07-27 Poly(arylaethersulfon)-zubereitungen mit verbesserten fliesseigenschaften.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/078,460 US4818803A (en) 1987-07-27 1987-07-27 Poly(aryl ether sulfone) compositions having improved flow properties
US078,460 1987-07-27

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EP (1) EP0327634B1 (fr)
JP (1) JPH02500849A (fr)
DE (1) DE3884373T2 (fr)
WO (1) WO1989001003A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008051651A1 (fr) * 2006-10-24 2008-05-02 Sabic Innovative Plastics Ip B.V. Compoitions de polyethersulfone ayant une resistance elevee a la chaleur et une bonne resistance aux impacts
KR101152067B1 (ko) 2004-09-27 2012-06-11 사빅 이노베이티브 플라스틱스 아이피 비.브이. 높은 내열성 및 양호한 내충격성을 갖는 폴리에테르설폰조성물

Families Citing this family (15)

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US4818803A (en) * 1987-07-27 1989-04-04 Amoco Corporation Poly(aryl ether sulfone) compositions having improved flow properties
US5164466A (en) * 1988-03-03 1992-11-17 Amoco Corporation Poly(aryl ether sulfone) compositions
US5086130A (en) * 1988-03-03 1992-02-04 Amoco Corporation Poly(aryl ether sulfone) compositions comprising poly(phenylene ether sulfone)
US5204442A (en) * 1991-02-06 1993-04-20 General Electric Company Polyether polymers derived from 4,4"-dihydroxy-m-terphenyls
EP1517960B1 (fr) * 2002-06-19 2008-12-10 Solvay Advanced Polymers, L.L.C. Isolation pour fil de bobinage comprenant un melange de polymeres de sulfone a temperature elevee
EP1526158A1 (fr) * 2004-12-22 2005-04-27 Solvay Advanced Polymers, L.L.C. Composition de polymère sulfone
TW200626672A (en) * 2004-10-04 2006-08-01 Solvay Advanced Polymers Llc High performance shaped articles, methods of making, and uses thereof
US20070117962A1 (en) * 2005-11-21 2007-05-24 General Electric Company High heat polyethersulfone compositions
US7273919B1 (en) * 2005-11-21 2007-09-25 General Electric Company High heat polyethersulfone compositions
CN100374483C (zh) * 2006-03-29 2008-03-12 长春吉大高科技股份有限公司 聚醚醚砜和聚醚醚酮三元共聚物的制备方法
BRPI0812908A2 (pt) * 2007-06-22 2014-12-09 Basf Se Composição de moldagem termoplástica, processo para a preparação de composições de moldagem termoplásticas, uso de composições de moldagem, e, corpo moldado, fibras, e folhas.
US9040651B2 (en) 2011-10-31 2015-05-26 Sabic Global Technologies B.V. Poly(aryl ether sulfone) composition, and method of making
US9534086B2 (en) * 2014-05-07 2017-01-03 International Business Machines Corporation Methods of forming poly(aryl ether sulfone)s and articles therefrom
US10059053B2 (en) 2014-11-04 2018-08-28 Stratasys, Inc. Break-away support material for additive manufacturing
CN108956382A (zh) * 2018-07-05 2018-12-07 大连工业大学 一种测定塑胶制品中邻苯二甲酸酯类增塑剂向气相迁移的方法

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US3647751A (en) * 1969-06-25 1972-03-07 Bayer Ag Polyarylether-sulphones
US4358569A (en) * 1980-12-31 1982-11-09 General Electric Company Blends of copolyester-carbonate with polysulfone
US4503168A (en) * 1983-05-25 1985-03-05 Union Carbide Corporation Cookware made from polyarylethersulfone

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US4520067A (en) * 1982-06-23 1985-05-28 Union Carbide Corporation Composition useful for making circuit board substrates and electrical connectors
CA1223389A (fr) * 1982-06-23 1987-06-23 James E. Harris Composition utile pour la fabrication de plaquettes a circuits integres et de connecteurs electriques
EP0215580A3 (fr) * 1985-08-19 1989-03-29 Union Carbide Corporation Mélanges miscibles de poly(aryléthersulfones)
US4818803A (en) * 1987-07-27 1989-04-04 Amoco Corporation Poly(aryl ether sulfone) compositions having improved flow properties

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US3634355A (en) * 1968-03-21 1972-01-11 Ici Ltd Aromatic polymers from dihalogenoben-zenoid compounds and alkali metal hydroxide
US3647751A (en) * 1969-06-25 1972-03-07 Bayer Ag Polyarylether-sulphones
US4358569A (en) * 1980-12-31 1982-11-09 General Electric Company Blends of copolyester-carbonate with polysulfone
US4503168A (en) * 1983-05-25 1985-03-05 Union Carbide Corporation Cookware made from polyarylethersulfone

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8106135B2 (en) 2004-09-27 2012-01-31 Sabic Innovative Plastics Ip B.V. Polyethersulfone compositions with high heat and good impact resistance
KR101152067B1 (ko) 2004-09-27 2012-06-11 사빅 이노베이티브 플라스틱스 아이피 비.브이. 높은 내열성 및 양호한 내충격성을 갖는 폴리에테르설폰조성물
US8623971B2 (en) 2004-09-27 2014-01-07 Sabic Innovative Plastics Ip B.V. Polyethersulfone compositions with high heat and good impact resistance
US8796399B2 (en) 2004-09-27 2014-08-05 Sabic Innovative Plastics Ip B.V. Polyethersulfone compositions with high heat and good impact resistance
WO2008051651A1 (fr) * 2006-10-24 2008-05-02 Sabic Innovative Plastics Ip B.V. Compoitions de polyethersulfone ayant une resistance elevee a la chaleur et une bonne resistance aux impacts

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DE3884373T2 (de) 1994-01-20
EP0327634B1 (fr) 1993-09-22
EP0327634A4 (en) 1990-09-05
US4818803A (en) 1989-04-04
EP0327634A1 (fr) 1989-08-16
JPH02500849A (ja) 1990-03-22
US4957978A (en) 1990-09-18
DE3884373D1 (de) 1993-10-28

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